WO1999033939A1 - Huile de malt d'orge contenant des substances vegetales associees a des ceramides, et procede de fabrication associe - Google Patents

Huile de malt d'orge contenant des substances vegetales associees a des ceramides, et procede de fabrication associe Download PDF

Info

Publication number
WO1999033939A1
WO1999033939A1 PCT/JP1998/005855 JP9805855W WO9933939A1 WO 1999033939 A1 WO1999033939 A1 WO 1999033939A1 JP 9805855 W JP9805855 W JP 9805855W WO 9933939 A1 WO9933939 A1 WO 9933939A1
Authority
WO
WIPO (PCT)
Prior art keywords
extract
ceramide
beer
barley malt
related substance
Prior art date
Application number
PCT/JP1998/005855
Other languages
English (en)
Japanese (ja)
Inventor
Hisao Kado
Fujio Kobayashi
Akira Hirota
Naoki Abe
Original Assignee
Sapporo Breweries Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sapporo Breweries Limited filed Critical Sapporo Breweries Limited
Priority to US09/355,982 priority Critical patent/US6316032B1/en
Priority to DE1998630985 priority patent/DE69830985T2/de
Priority to EP19980961516 priority patent/EP0969079B1/fr
Priority to CA 2281910 priority patent/CA2281910C/fr
Publication of WO1999033939A1 publication Critical patent/WO1999033939A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/899—Poaceae or Gramineae (Grass family), e.g. bamboo, corn or sugar cane
    • A61K36/8998—Hordeum (barley)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/10—Production of fats or fatty oils from raw materials by extracting
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/85—Products or compounds obtained by fermentation, e.g. yoghurt, beer, wine
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes

Definitions

  • the present invention relates to a barley malt oil containing a plant ceramide-related substance and a method for producing the same. Specifically, the present invention relates to a barley malt oil containing a plant ceramide-related substance derived from beer lees obtained in a beer production process. The present invention relates to a method for easily producing barley malt oil. Background art
  • ceramide-related substances such as ceramide and cerebroside (ceramide glycolipid) may have a high moisturizing effect. It was revealed. In addition, it has become known that these ceramide-related substances are abundant in the stratum corneum of human skin and function to prevent evaporation of water from the body.
  • the ceramide-related substance has a function of inhibiting the entry of antigens into the body from the outside world and a function of exhibiting an effect on atopic dermatitis.
  • ceramide-related substances have recently been developed as pharmaceuticals.
  • ceramide-related substances have been extracted and supplied from the brain or spinal cord of cattle.
  • the supply has been drastically reduced, and it is necessary to secure alternative raw materials.
  • plant ceramide-related substances are those derived from rice (Agric. Biol. Chem., 49, 2753 (1985)) and wheat (Agric. Biol. Chem., 49, 3609 (1985)).
  • plant ceramide-related substances derived from these grains are already being developed as cosmetic materials.
  • the present invention solves the above-mentioned conventional drawbacks, and provides a method for efficiently and easily obtaining barley malt oil which is high in safety and which is rich in plant-derived ceramide-related substances of good plant origin as a material. The purpose is to do so.
  • Another object of the present invention is to provide a barley malt oil which is obtained by such a method and which is rich in plant cellamide-related substances with high safety. is there.
  • beer meal generated quantitatively during beer production is currently mainly used as feed.
  • beer lees can be extremely suitably used as a raw material for producing a plant ceramide-related substance.
  • beer cake contains a large amount of lipid (about 10% in dry matter), and this lipid contains high value-added plants such as cosmetics and pharmaceutical materials. It has been found that a large amount of ceramide-related substances is present, and that beer lees can be used very suitably as a raw material for the production of plant ceramide-related substances.
  • beer lees contain most of the lipids contained in raw materials for beer production, such as malt, and contain a very large amount of lipids, about 10% per dry matter weight.o
  • the lipid component contained in the beer lees contains a large amount of plant ceramide-related substances.
  • Beer meal is a by-product that is quantitatively generated during the production of beer, but since it has already been heated when producing wort for beer, heat-unstable lipids have been removed.
  • fatty acid esters are hydrolyzed and converted to free fatty acids by the action of lipase expressed when barley germinates.
  • beer lees are used as a raw material for vegetable ceramide-related substances instead of rice wheat, the step of separating such unnecessary substances can be omitted, and the plant ceramide-related substances can be very easily abundant. Can be obtained.
  • beer meal is a by-product of food production derived from plants, so it can always be supplied with safe and stable quality.
  • beer lees can be used very suitably as a raw material for producing plant ceramide-related substances.
  • the present invention has been made based on the above findings, and provides a method for producing a plant ceramide-related substance contained in beer lees by a simple method. Disclosure of the invention
  • the present invention described in claim 1 includes a step of immersing beer cake obtained in a beer production process in a polar organic solvent, a step of separating an extract from the immersion solution, And a method for producing barley malt oil containing a botanical ceramide-related substance, comprising the step of: O
  • the residue obtained in the step of separating the extract from the immersion solution is immersed in a polar organic solvent. Thereafter, the extract is separated from the soaking solution, and the extract and the extract obtained above are mixed and concentrated for treatment.
  • a method for producing malt oil is provided.
  • the concentrate obtained in the concentration treatment step is converted to a mixed solvent of a halogenated organic solvent and alcohol.
  • the concentrate obtained in the concentration treatment step is dissolved in a mixed solvent of a halogenated organic solvent and alcohol.
  • the barley malt oil containing the plant ceramide-related substance according to claim 2 further comprising: a step of separating and removing insolubles; and a step of concentrating the solution obtained in the step of separating and removing.
  • the invention according to claim 5 is the method according to claim 4, wherein the solvent obtained by the final concentration treatment step is subjected to a solvent fractionation step.
  • An object of the present invention is to provide a method for producing barley malt oil containing a plant ceramide-related substance.
  • An object of the present invention is to provide a barley malt oil containing a plant ceramide-related substance obtained by subjecting a discharged liquid to a concentration treatment.
  • the present invention according to claim 1 relates to a method for producing barley malt oil containing a plant ceramide-related substance, wherein a step of immersing beer cake obtained in a beer production process in a polar organic solvent is provided. A step of separating an extract from the immersion solution; and a step of concentrating the extract.
  • the beer meal as a raw material is a by-product generated when wort is obtained in the process of producing beer.
  • Beer cake is usually generated with a large amount of water (about 90% water).
  • the beer cake in the water-containing state water content of about 90%
  • the water content may be reduced to about 60 to 65% by a dehydrator such as a cylinder press or a filter press. Any of reduced forms, such as dried beer lees (water content of about 0 to 20%), may be used.
  • drying under conditions that are exposed to high heat denatures the target substance due to heat, so that the temperature is not very high (for example, 60 to 100 ° C). (° C) is preferably used.
  • the drying treatment is performed with a dehydrator, there is a possibility that some of the target substance may leak together with water, and the yield may decrease. Therefore, it is better to refrain from using a dehydrator. Therefore, usually, as the raw material beer lees, the water-containing beer lees discharged from the process is most preferably used.
  • the portion having a high lipid content is a portion having a relatively small particle size in the beer meal, it can be collected by a conventional method such as filtration using a sieve, a coarse cloth, or paper.
  • the raw material beer cake
  • a polar organic solvent Through this immersion step, the target substance, a plant ceramide-related substance, is extracted.
  • the polar organic solvent used in this immersion step may be any solvent having a polarity such as alcohol, black form, and acetone, but an alcohol having high hydrophilicity is particularly preferable.
  • any one which shows polarity and can be mixed with water such as methanol, ethanol, propanol, isopropanol and butanol, can be used.
  • methanol is most preferably used in consideration of the production cost or the solvent removal step by concentration described below.
  • the amount of the polar organic solvent to be used is not particularly limited. However, if the amount is small, inconveniences such as the necessity of performing the filtration operation under pressure occur. In order to liquefy the mixture of the polar organic solvent and the beer lees and allow natural filtration, it is preferable to add the beer lees in an amount at least three times the weight of the beer lees. On the other hand, the amount of polar organic solvent The limit is not particularly limited, and if economically acceptable, it is better to add a large amount. When alcohol is used as the polar organic solvent, it is preferable that about 10 to 20% of water be present. It is for such a reason that the hydrous beer lees discharged from the process can be most suitably used as the raw material used in the method of the present invention.
  • the immersion time is not particularly limited, but is about 1 to 15 hours, so that the target substance can be sufficiently extracted.
  • the time required for this immersion can be reduced by stirring the solvent.
  • the extract is separated from the immersion solution. That is, the extracted soluble substance is separated from the immersed solution of the polar organic solvent.
  • the method of separation is not particularly limited.
  • the separation can be performed using a press fill, a cylinder press, a screw decanter, or the like.
  • the extract separated from the immersion solution in this way is then sent to a concentration treatment step.
  • the residue obtained in the step of separating the extract from the immersion solution is immersed again in a polar organic solvent, and then the extract is separated from the immersion solution.
  • the extract can be mixed with the extract obtained above, and the mixture can be sent to the next concentration treatment step. According to such a method, the extraction efficiency can be further increased.
  • beer cake for example, water-containing beer cake with a water content of about 90%
  • a polar organic solvent of 3 times or more, extracted, and then extracted.
  • the extraction efficiency is improved by re-extracting the residue with the same amount of polar organic solvent. Can be raised.
  • the concentration process may be performed using, for example, a rotary evaporator.
  • a concentrate that is a brownish oily substance that is, a barley malt oil containing a target vegetable ceramide-related substance
  • the purity of the plant ceramide-related substance can be further improved.
  • the concentrate obtained in the concentration treatment step is dissolved in a mixed solvent of a halogenated organic solvent and alcohol.
  • water-soluble substances such as carbohydrates and inorganic salts are removed by dissolving the concentrate (oil-like substance) obtained as described above in a halogen-based organic solvent-methanol mixed solvent and removing insolubles. can do.
  • chloroform-form chloroform-form, dichloromethane, and the like are effective.
  • the mixture ratio of black form and methanol is 5: 5 to 9: 1 (volume ratio). Is preferable from the viewpoint of sufficiently dissolving the ceramide-related substance.
  • the concentration process may be performed using, for example, a mouthful or an evaporator.
  • washing with a solvent such as hexane or ether can remove low-polar impurities such as fatty acid esters.
  • the concentrate obtained in the concentration treatment step is dissolved in a mixed solvent of a halogenated organic solvent and alcohol. Then, a step of separating and removing insolubles and a step of concentrating the solution obtained in the step of separating and removing can be further performed.
  • the concentrate obtained at this time contains 10% or more of a plant ceramide-related substance, and satisfies the object of the present invention.
  • Examples of the method for the decolorization treatment include solvent fractionation or treatment with activated carbon, a hydrophobic resin, or the like.
  • solvent fractionation is a method of reducing the degree of coloring by utilizing the difference in solubility between the target substance and the coloring component in a solvent.
  • any solvent can be used as long as the target substance is insoluble but the coloring component is soluble, and the alcohols previously used for extraction are suitably used.
  • a solvent such as acetone or ethyl acetate alone or in a mixture as appropriate.
  • solvent fractionation for example, add methanol and gently heat to solubilize the target substance, filter while hot, remove insolubles, gradually lower the temperature, and finally o ° When left at a temperature of c or less for several hours to several days, a pale yellow precipitate is deposited. In this way, it is possible to reduce the degree of coloring and improve the purity of the plant ceramide-related substance.
  • a treatment with activated carbon a hydrophobic resin, etc.
  • a hydrophobic resin such as Amberlite HP series can be suitably used as a carrier in the case of resin treatment.
  • the purity of the plant-ceramide-related substance can be further improved by chromatography using a silica gel column and / or preparative high-performance liquid chromatography.
  • barley malt oil containing a plant ceramide-related substance can be obtained.
  • the present invention described in claim 6 provides a barley malt oil containing such a plant ceramide-related substance.
  • the present invention described in claim 6 was obtained in a beer manufacturing process.
  • a barley malt oil containing a plant ceramide-related substance obtained by immersing beer cake in a polar organic solvent, separating an extract from the solution, and concentrating the extract. Specifically, it can be obtained by the present invention described in claim 1. Accordingly, for example, the type of the polar organic solvent and the immersion conditions are as described in the description of the present invention described in claim 1. It should be noted that, with respect to the present invention described in claim 6, the barley malt oil containing a plant ceramide-related substance obtained as described in the present invention described in claims 2 to 5 is also used. Can be included.
  • the barley malt oil of the present invention described in claim 6 thus obtained contains abundant vegetable ceramide-related substances (10% by weight or more based on the whole), and can be purified and fractionated. By repeating, the purity can be raised to about 90%.
  • the ceramide-related substance derived from beer lees obtained as described above has a structure similar to that of other vegetable oil-derived ceramide-related substances such as wheat and rice, and has the same effect as moisturizing effect. Therefore, it can be used as a raw material for cosmetics by blending it into creams and emulsions. In addition, it can be used as a pharmaceutical raw material.
  • the present invention will be described specifically with reference to Examples, but the present invention is not limited thereto.
  • the first and second extracts were combined, and concentrated by evaporation and evaporation to obtain 8.7 kg of concentrate (lipid) from beer lees lk.
  • Table 1 shows the ceramide-related substance purity of the obtained powder.
  • Example 2 0.5 g of the pale brown powder obtained in Example 2 was dissolved in 5 mL of a mixed solvent of formaldehyde and methanol (2: 1). Then, a mixed solvent of form-methanol (9: 1) was previously passed through the same silica gel column used in Example 2 to sufficiently stabilize (equilibrate), and the column was charged. Aliquot the aliquot into aliquots and use silica gel thin-layer chromatography. The fractions showing the presence of plant ceramide-related substances were collected, and the solvent was removed by rotary evaporation overnight.
  • Table 1 shows the ceramide-related substance purity of the obtained powder.
  • Example 3 0.1 lg of the pale yellow powder obtained in Example 3 was dissolved in 0.5 mL of a mixed solvent of formaldehyde and methanol (2: 1), and a high-performance liquid using a preparative silica gel column. Further purification was performed by a chromatographic system using a forward layer chromatography using a hexane-methanol mixture as an eluent.
  • the eluate from the column was monitored with an ultraviolet detector at a wavelength of 205 nm, the peaks were collected, thin layer chromatography was performed, and the plant ceramide-related substances were collected. The solvent was removed.
  • Example 1 1 g of the brown powder obtained in Example 1 was charged into a medium heated to about 60 ° C. while stirring. While maintaining the temperature as it was, the mixture was filtered using filter paper to remove insolubles, then the temperature was gradually lowered, and the mixture was allowed to stand overnight at 20 C. The obtained precipitates were collected, poured again into methanol heated to about 60 ° C, and the same operation was performed.
  • Table 1 shows the ceramide-related substance purity of the obtained powder.
  • the barley malt oil which has high safety and which is rich in a plant ceramide-related substance originating from a plant with good image quality can be efficiently obtained.
  • beer lees as a raw material is a by-product of food production derived from plants, so it is always safe to supply it with stable quality.
  • barley malt oil is provided which is rich in a plant-ceramide-related substance with high safety.
  • the present invention can be effectively used in the fields of cosmetics and pharmaceuticals.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Birds (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Botany (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biotechnology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Molecular Biology (AREA)
  • Medical Informatics (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Biophysics (AREA)
  • Dermatology (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Cosmetics (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Fats And Perfumes (AREA)
  • Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

Procédé permettant d'obtenir efficacement et simplement de l'huile de malt d'orge riche en substances végétales associées à des céramides, présentant une parfaite innocuité et extraites de plantes ayant une image favorable; et huile de malt d'orge obtenue par ledit procédé, riche en substance végétales associées à des céramides présentant une parfaite innocuité. Le procédé est caractérisé par les étapes suivantes: on plonge dans un solvant polaire organique le tourteau de bière obtenu lors de la production de bière, on sépare l'extrait de la solution d'immersion et on le concentre. On obtient l'huile de malt d'orge en plongeant dans un solvant organique le tourteau de bière obtenu lors de la production de bière, en séparant l'extrait de la solution d'immersion et en le concentrant.
PCT/JP1998/005855 1997-12-26 1998-12-24 Huile de malt d'orge contenant des substances vegetales associees a des ceramides, et procede de fabrication associe WO1999033939A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US09/355,982 US6316032B1 (en) 1997-12-26 1998-12-24 Barley malt oil containing vegetable ceramide-associated substances and process for producing the same
DE1998630985 DE69830985T2 (de) 1997-12-26 1998-12-24 Gerstenmalzöl enthaltend mit ceramid assoziierte pflanzliche substanzen sowie verfahren zu ihrer herstellung
EP19980961516 EP0969079B1 (fr) 1997-12-26 1998-12-24 Huile de malt d'orge contenant des substances vegetales associees a des ceramides, et procede de fabrication associe
CA 2281910 CA2281910C (fr) 1997-12-26 1998-12-24 Huile de malt comprenant des derives de ceramide et leur methode de production

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP9/366876 1997-12-26
JP36687697A JPH11193238A (ja) 1997-12-26 1997-12-26 植物性セラミド関連物質を含有する大麦麦芽油及びその製造方法

Publications (1)

Publication Number Publication Date
WO1999033939A1 true WO1999033939A1 (fr) 1999-07-08

Family

ID=18487913

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1998/005855 WO1999033939A1 (fr) 1997-12-26 1998-12-24 Huile de malt d'orge contenant des substances vegetales associees a des ceramides, et procede de fabrication associe

Country Status (6)

Country Link
US (1) US6316032B1 (fr)
EP (1) EP0969079B1 (fr)
JP (1) JPH11193238A (fr)
CA (1) CA2281910C (fr)
DE (1) DE69830985T2 (fr)
WO (1) WO1999033939A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002005662A1 (fr) * 2000-07-19 2002-01-24 Unitika Ltd. Produits de beaute ou aliments physiologiquement fonctionnels contenant des sphingoglycolipides et procedes permettant de les fabriquer

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3650587B2 (ja) * 2001-03-26 2005-05-18 ユニチカ株式会社 スフィンゴ糖脂質を含有する機能性食品及びその製造方法
JP2006096961A (ja) * 2004-09-30 2006-04-13 Sapporo Breweries Ltd 植物性スフィンゴ糖脂質含有油の製造方法
JPWO2007069733A1 (ja) * 2005-12-16 2009-05-28 株式会社ディーエヌエーバンク・リテイル アルカリ水溶液を用いたセラミド関連物質の製造方法とその装置
JP5392451B2 (ja) 2005-12-27 2014-01-22 国立大学法人 琉球大学 抗腫瘍剤及び免疫賦活剤
US8518673B2 (en) 2007-06-29 2013-08-27 Kfi Intellectual Properties L.L.C. Method for extracting oil from a water and solids composition
JP2012126910A (ja) * 2010-07-23 2012-07-05 Miyanabe Masakatsu 発酵粕由来スフィンゴ脂質
JP5013348B2 (ja) * 2010-07-23 2012-08-29 宮鍋 征克 スフィンゴ脂質の取得方法
ES2489295B1 (es) * 2013-02-21 2015-07-22 Maria Del Pino PEREZ ALVAREZ-CASTELLANOS Procedimiento para el aprovechamiento de los subproductos de la industria cervecera mediante la obtención de aceite con uso biocombustible
CN111060644A (zh) * 2019-09-26 2020-04-24 吕梁学院 应用tlc-cms-ir检测米糠神经酰胺类化合物的方法
WO2023096450A1 (fr) * 2021-11-26 2023-06-01 주식회사 라피끄 Composition cosmétique à base de drêche de brasserie et procédé de fabrication associé

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03123479A (ja) * 1988-11-18 1991-05-27 Kirin Brewery Co Ltd ビール粕から高タンパク質含有物、繊維質及び／又は植物油を製造する方法
JPH0530981A (ja) * 1991-07-25 1993-02-09 Ngk Insulators Ltd 酵母抽出油脂の製造方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1310399A (en) * 1970-10-23 1973-03-21 Le Teknologichesky I Kholodiln Method of preparing an antibacterial and antimycotic preparation
BE758084A (fr) * 1970-10-27 1971-04-27 Le Teknologichesky I Kholodiln Produit bactericide et mycostatique et son procede de preparation
US4804545A (en) * 1984-08-10 1989-02-14 Barco, Inc. Production of beta-glucan, bran, protein, oil and maltose syrup from waxy barley
CA1242160A (fr) * 1984-08-10 1988-09-20 Kenneth J. Goering Procede de recuperation de produits de l'orge
US5013561A (en) * 1984-08-10 1991-05-07 Barco, Inc. Process for recovery of products from waxy barley
RU1776407C (ru) * 1990-09-21 1992-11-23 Научно-производственное объединение "Аэрозоль" Крем-бальзам дл ухода за кожей лица
FR2676936B1 (fr) * 1991-05-27 1993-11-05 Inocosm Laboratoires Procede de separation d'un compose riche en glycolipides lysophospholipides shingolipides et ceramides d'origine vegetale, ainsi que produits cosmetiques obtenus par la mise en óoeuvre de ce procede.
JP3123479B2 (ja) 1996-09-26 2001-01-09 松下電器産業株式会社 ハロゲンコンロ

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03123479A (ja) * 1988-11-18 1991-05-27 Kirin Brewery Co Ltd ビール粕から高タンパク質含有物、繊維質及び／又は植物油を製造する方法
JPH0530981A (ja) * 1991-07-25 1993-02-09 Ngk Insulators Ltd 酵母抽出油脂の製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0969079A4 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002005662A1 (fr) * 2000-07-19 2002-01-24 Unitika Ltd. Produits de beaute ou aliments physiologiquement fonctionnels contenant des sphingoglycolipides et procedes permettant de les fabriquer
US6896896B2 (en) * 2000-07-19 2005-05-24 Unitika Ltd. Physiologically functional foods or cosmetics containing sphingoglycolipids and processes for their production
KR100855199B1 (ko) * 2000-07-19 2008-09-01 유니티카 가부시끼가이샤 스핑고당지질을 함유하는 기능성 식품 및 이의 제조방법

Also Published As

Publication number Publication date
CA2281910A1 (fr) 1999-07-08
EP0969079B1 (fr) 2005-07-27
CA2281910C (fr) 2009-05-12
US6316032B1 (en) 2001-11-13
EP0969079A1 (fr) 2000-01-05
JPH11193238A (ja) 1999-07-21
EP0969079A4 (fr) 2003-06-04
DE69830985T2 (de) 2006-04-20
DE69830985D1 (de) 2005-09-01

Similar Documents

Publication Publication Date Title
US5705618A (en) Process for extracting lignans from flaxseed
US6740778B2 (en) Method for the preparation of oleanolic acid and/or maslinic acid
JPS58192828A (ja) 栄養組成物およびその製造法
JP5013348B2 (ja) スフィンゴ脂質の取得方法
CN102648271B (zh) 从可再生的原材料中提取不皂化物的方法
WO1999033939A1 (fr) Huile de malt d'orge contenant des substances vegetales associees a des ceramides, et procede de fabrication associe
US7109384B2 (en) Process to extract phenolic compounds from a residual plant material using a hydrothermal treatment
WO2009116264A1 (fr) Son de céréale sec dégraissé contenant un ingrédient diététique adsorbé et concentré, concentré d'ingrédient diététique préparé à partir du son et son procédé de fabrication
JPH0873396A (ja) 天然メナキノン−７高含量脂質
JP4883449B2 (ja) セラミド類含有組成物およびその製造方法
JP6273551B2 (ja) アミロイド形成阻害作用を呈するネルボン酸誘導体
JP4503263B2 (ja) スフィンゴ糖脂質の製造方法
JP3665298B2 (ja) トリテルペンの抽出法
JP2007082427A (ja) ビール粕由来の植物性セラミド関連物質製造方法
JP3992425B2 (ja) スフィンゴ糖脂質含有物の製造方法
JP2001097983A (ja) スフィンゴ脂質を含有する植物抽出物およびその製造方法
JPH03227985A (ja) イチョウ葉からフラボノイドを高含有する抽出物の簡易な製造法
JP6292072B2 (ja) ヒアルロン酸合成酵素誘導作用を呈する脂肪酸誘導体及びその製造方法
EP0137862B1 (fr) Procédé de préparation de corps gras
JP7245966B2 (ja) ＡＧＥｓ吸着作用を呈するスフィンゴシン誘導体
JP2005343814A (ja) 天然物由来グリセロ糖脂質の製造方法
EP3253229B1 (fr) Procédé pour le fractionnement de graines de plantes oléagineuses
JPH09235549A (ja) 抗酸化剤
JP4326720B2 (ja) こんにゃく抽出物及びその製造方法
JP6738524B2 (ja) 酸化的リン酸化の活性化作用を呈するロイコシアニジン誘導体

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

ENP Entry into the national phase

Ref document number: 2281910

Country of ref document: CA

Ref country code: CA

Ref document number: 2281910

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: 09355982

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 1998961516

Country of ref document: EP

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWP Wipo information: published in national office

Ref document number: 1998961516

Country of ref document: EP

WWG Wipo information: grant in national office

Ref document number: 1998961516

Country of ref document: EP